Dichloromethane → HCID 61645017, compound

HRID 594375Notes

Reaction equation

HRID 594375 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([O:15][CH3:16])[CH:8]=1.Cl[C:18](=[O:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22].C(Cl)Cl>ClCCCl>[O:25]=[C:18]([C:8]1[C:9]([O:15][CH3:16])=[CH:10][C:11]([O:13][CH3:14])=[CH:12][C:7]=1[O:6][CH3:5])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 693011,3,5-TrimethoxybenzeneHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 6451240Aluminum(III) Chloride

Product 1

HCID 61645017HCID 61645017, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) suspension of AlCl3 (2.036 g; 15.27 mmol) in anh. DCE (10 ml) was treated with commercially available 1,3,5-trimethoxybenzene (1.675 g; 9.96 mmol), and stirring at 0° C., under nitrogen, was continued for 10 min. Commercially available methyl 4-chloro-4-oxobutanoate (1.000 g; 6.64 mmol) was then added, and the mixture was stirred at rt for 24 h. The resulting reaction mixture was poured onto crushed ice (30 g), and DCM (20 ml) was added. The separated aq. layer was further extracted with DCM (3×10 ml). The mixed organic layers were washed successively with water (15 ml) and brine (2×15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording methyl 4-oxo-4-(2,4,6-trimethoxyphenyl)butanoate as a colorless oil. LC-MS (conditions D): tR=0.88 min.; [M+H]+: 283.02 g/mol.

Workup

  1. temperatureA cooled
  2. stirringthe mixture was stirred at rt for 24 h
  3. customThe resulting reaction mixture
  4. additionwas poured
  5. additionwas added
  6. extractionThe separated aq. layer was further extracted with DCM (3×10 ml)
  7. washThe mixed organic layers were washed successively with water (15 ml) and brine (2×15 ml)
  8. dry with materialdried over anh. MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f35a3b5cf2b94c7dac880db34592b80e
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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